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The ultimate guide to men’s dress boots
Why every man needs a pair of dress boots
As the saying goes, clothes make the man. That applies to your outfit, your accessories, and your choice of footwear.
The best dress boots for men offer versatility and sophistication. By choosing the right varieties, materials, and colors, you can demonstrate arresting style and poise in any occasion – especially when others simply default to shoes.
For more than 35 years, Martin Dingman has crafted premium men’s footwear that blends refined country life with rugged Ozark spirit. With world-class craftsmanship and exemplary materials, we’ve developed a reputation as one of America’s finest leather goods brands, catering exclusively to the discerning modern gentleman.
The essential types of men’s dress boots
Each type of men’s dress boot has its own signature qualities, and suits different settings. Here are the core breeds that every man of culture should own.
Chelsea boots
With no laces and a single seam, these minimalist slip-on men’s dress boots deliver effortless style. Made fashionable in the 60s by The Beatles and other British rock bands, Chelsea boots have remained an essential wardrobe staple ever since.
Chukka boots
Characterized by their few eyelets, thin laces, and open-laced design, chukka boots offer the perfect balance between casual and dressy. They’re a versatile option that adds a simple touch of class and elegance to everything from dress-down meetings to weekend recreation.
Lace-up boots
The modern silhouette of classic lace-up boots makes them a structured, sophisticated option for men’s formalwear. Whether a day at the office or an exclusive soiree, this tasteful and comfortable footwear adds the finishing touch to a sharp outfit.
How to choose the right dress boots for your style
Choosing the right type of men’s dress boots is only the first step. It’s also important to tailor the characteristics of your footwear to the occasion.
Material matters
Premium men’s dress boots typically come in one of two materials:
- Full-grain leather: A classic powerhouse that polishes up for a mirror shine. Leather dress boots always look sharp and work as both formal and informal wear.
- Suede: Suitable for smart-casual to semi-formal, suede’s soft texture and matte finish add visual appeal. Flexible and comfortable from the first wear.
Color selection
Dress boots come in a range of colors. But only two lend themselves to classic style:
- Black: The most formal color, essential for business settings and black-tie events. Cap toe boots are a classic choice, but you can lighten the mood with wingtip or bicycle-toe designs.
- Brown: Extremely flexible. Choose light browns like tan or whiskey for casual settings, and darker shades such as espresso or mahogany for more formal affairs
Material matters
Dress for the occasion
- Work: Classic lace-up boots are always a safe choice, closely followed by sleek Chelsea boots. Save chukkas for business-casual settings.
- Weekend: Versatile chukka boots pair well with most casual outfits. Opt for brown suede Chelsea boots to add a little extra touch of class.
How to style men’s dress boots for different outfits
To achieve a cohesive look it’s important to match men’s dress boots with the right outfit. Take a look at these foolproof suggestions to get started.
Polished but flexible business casual
Edge toward business with hand-finished Napoli Italian Saddle Leather Boots. Pair with dark tailored trousers, a fine-gauge sweater, and a blazer.
On the more casual end, pick Blue Ridge Suede Chelsea Boots. These go with slim wool trousers, a tucked-in dress shirt, and an unstructured blazer. Remember that Chelsea boots best suit straight- or slim-fit clothing.
Relaxed weekend smart-casual style
Chukka boots are ideal for a tasteful weekend look. Try Blue Ridge Suede Chukka Boots with slim chinos, a crewneck tee, and a cardigan or bomber jacket.
If chukkas aren’t your style, go with Windsor Oiled Saddle Leather Chelsea Boots. Combine with slim dark jeans, a Henley shirt or knit polo, and a leather jacket. Add extra flair by rolling your jeans slightly over the boot.
Refined formal and evening wear
A man of supreme style, confidence, and standing can buck tradition with rich, deep brown lace-up boots like Napoli Italian Suede Leather Boots. Wear a charcoal suit - not black - but otherwise follow expectations with a crisp dress white shirt and silk tie.
For less formal events, Windsor Saddle Chelsea Boots pair well with a slim-fit black suit, white shirt, and black silk tie. Your pants should kiss the top of the boots, not bunch over them.
Rugged chic for the great outdoors
Waterproof Laverack Oiled Saddle Leather Field Boots with heavy chinos, a wool sweater, and a field jacket gives you a refined country look. Choose earth tones or muted colors to suit the outdoors, and add leather gloves and a rough scarf if it’s chilly.
Leather or waxed suede chukkas also suit rougher weather, though they look better when properly broken in. Grab a pair of comfortable Blue Ridge Water Buffalo Chukka Boots to go with straight-fit jeans, a flannel shirt, and a quilted vest.
Leather dress boot care and maintenance tips
Men’s leather dress boots aren’t just a purchase – they’re an investment. With the proper care and maintenance, they offer a lifetime of sophistication and elegance.
Leather-care essentials
Leather’s suppleness, durability, and breathability comes from its status as an organic material. As such, premium dress boots need cleaning, polishing, and conditioning to maintain their quality.
- Insert dry leather dress boots into a pair of cedar shoe trees
- Use a soft brush and damp cloth to gently clean away dirt
- Polish with a specialized brush and a small amount of leather cleaner
- Allow them to dry overnight, then buff with a horsehair brush
- Condition using a dab of leather cleaner and a microfiber cloth
For other materials, see our full shoe care guide.
Protecting against the weather
Leather is naturally water resistant. But it can’t survive excessive water exposure. So it’s important to treat men’s leather dress boots to prevent mold or rot.
- Apply an even coat of leather-specific waterproofing spray
- Gently work it into the material with a soft microfiber cloth
- Repeat two or three times to ensure adequate protection
Shoe trees and storage
Before storing leather dress boots, allow them to dry naturally for 24-48 hours. Then insert a pair of wooden shoe trees to maintain structure and wick away excess moisture. Store your boots in their original box to ensure proper ventilation.
Elevate your footwear with Martin Dingman
Investing in a pair of premium men’s boots empowers the modern gentleman to command respect and admiration – both in business and on his day off.
With peerless craftsmanship, the finest materials, and meticulous attention to detail, Martin Dingman boots deliver unquestionable style and gravitas for the cultured modern man.
Shop Martin Dingman’s handcrafted dress boots today and choose from more than 300 footwear products in genuine leather and quality suede.
